CN116283937A - 一种光催化合成芳基仲胺类化合物的方法 - Google Patents

一种光催化合成芳基仲胺类化合物的方法 Download PDF

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CN116283937A
CN116283937A CN202310364042.2A CN202310364042A CN116283937A CN 116283937 A CN116283937 A CN 116283937A CN 202310364042 A CN202310364042 A CN 202310364042A CN 116283937 A CN116283937 A CN 116283937A
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张卫东
张宇
王金鑫
李倩楠
李艳川
赵新才
蔡观
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Abstract

本发明公开了一种光催化合成芳基仲胺类化合物的方法，属于化学合成技术领域。惰性气体保护下，以对甲苯磺酰腙衍生物1和胺2为原料，在碱存在下，有机溶剂中将反应管427nm光源下照射4‑20小时，分离纯化后得到芳基仲胺类化合物3；本发明反应关键为通过缓慢释放供体/供体重氮物质，随后与多功能胺反应以实现N‑H插入；原料廉价易得，操作简单，绿色环保，为N‑H插入合成胺类化合物提供了一条新途径，同时该策略还可以应用于β‑氨基酸的构建。

Description

一种光催化合成芳基仲胺类化合物的方法
技术领域
本发明属于有机合成技术领域，具体涉及一种光催化合成芳基仲胺类化合物的方法。
背景技术
众所周知，含氮分子(如氨基酸、生物碱以及N-杂环化合物)具有广泛生物和药理活性。据报道，超过85％ FDA批准的药物都含有氮原子，且氮杂环百分比和频率继续增加。多功能胺类产物是天然产品中普遍存在的骨架。因此，开发简便和可持续的策略来引入C-N键合成胺类化合物成为高需求。
近些年来，化学家们努力开发简单多样的策略来引入C-N键，例如eTM催化C-N交叉偶联反应，还原胺化和亲电胺化，由Buchwald和Hartwig开发的钯催化Csp2-N偶联是最常用引入C-N键的方法。
此外，基于卡宾N-H插入形成C(sp3)-N键发展迅速，通常金属类卡宾首先由重氮或重氮前体形成，随后与具有N-H键的分子反应生成N-H插入产物。然而，铑、铜、钌、银和铁催化剂等金属催化剂对于生成金属类卡宾和促进反应不可或缺，且底物范围相对限于烷基重氮酯。同时，由于这些分子的不稳定性和不可用性，没有吸电子基团的供体和供体/供体型重氮化合物很少被应用于基于卡宾的N-H插入中，从而导致含氮分子的结构多样性比较差。
因此，开发更可持续和良性的方法来实现C-N键的形成，而无需金属催化剂，并且具有广泛的底物范围，包括供体型重氮化合物或前体。
发明内容
本发明基于上述研究进行，目的在于提供一种安全、绿色、高效的光催化实现N-H插入合成芳基仲胺类化合物的方法。惰性气体保护下，以对甲苯磺酰腙衍生物和胺为原料，在碱存在下，有机溶剂中光源下照射反应，分离纯化后得到芳基仲胺类化合物；本发明能够缓慢释放供体/供体重氮物质，随后与多功能胺反应以实现N-H插入；原料廉价易得，操作简单，绿色环保，为N-H插入合成胺类化合物提供了一条新途径，同时该策略还可以应用于β-氨基酸的构建。
为了实现上述目的，本发明所采用的技术方案如下：
本发明以酮、对甲基苯磺酰肼、胺和碱为原料，或直接以对甲苯磺酰腙衍生物、胺、碱为原料通过光催化方式得到产物实现N-H插入胺类化合物。两种原料合成实现N-H插入产物的方式基本相同，仅采用第一种原料时，先进行酮、对甲基苯磺酰肼间的密封搅拌，然后进行合成过程。
本发明所述一种光催化合成芳基仲胺类化合物的方法，包括如下步骤：以对甲苯磺酰腙衍生物1和胺2为原料，在碱存在下，有机溶剂中光照反应，得到芳基仲胺类化合物3。
反应方程式如下：
Figure BDA0004166000560000021
其中：
所述对甲苯磺酰腙衍生物1中，R1和R2各自独立选自H、C1-C4烷基、苄基及其取代物、苯基呋喃及其取代物、苯并噻吩及其取代物、吲哚及其取代物、苯基及其取代物、萘基及其取代物；取代物为C1-C4烷基、C1-C4烷氧基、C1-C4烷氧羰基烷氧基、亚甲基二氧基、Boc、卤素、苯氧基；或R1-R2一起通过碳、氧、硫或氮原子组成环状结构；
所述胺2中，R3和R4各自独立选自H、C1-C6烷基、烯丙基、苄基、苯基/联苯基及其取代物、吡啶及其取代物、喹啉/喹喔啉及其取代物、嘧啶及其取代物；取代物为C1-C4烷基、C1-C4烷氧基、N-Boc哌嗪、卤素；或R1-R2一起通过碳、氧、硫或氮原子组成环状结构。
进一步地，在上述技术方案中，所述对甲苯磺酰腙衍生物1典型结构为：
Figure BDA0004166000560000022
进一步地，在上述技术方案中，所述胺21典型结构为：
Figure BDA0004166000560000031
进一步地，在上述技术方案中，所述碱选自DBU、DBN、DABCO、DTHP、Cs2CO3、K2CO3、K2PO4、Na2CO3或NaHCO3中的一种或多种。反应发生的关键为经过电子供体-受体(EDA)络合物的过程；采用UV/Vis吸收谱检测，发现最合适的碱为DBN、TBD、DBU或Cs2CO3。
进一步地，在上述技术方案中，所述有机溶剂选自γ-戊内酯、二氯甲烷、乙腈、四氢呋喃及乙酸乙酯中的任意一种或多种组合。优选有机溶剂为二氯甲烷。
进一步地，在上述技术方案中，对甲苯磺酰腙衍生物1、胺2与碱摩尔比为1:1-10:1-3。
进一步地，在上述技术方案中，反应温度为20-35℃；反应时间为4-20小时。
进一步地，在上述技术方案中，光源波长为400-460nm；光源距离反应管为2-6厘米。
进一步地，在上述技术方案中，反应在惰性氛围下进行。
进一步地，在上述技术方案中，所述对甲苯磺酰腙衍生物1采用羰基化合物(醛或酮)与对甲苯璜酰肼在醇类溶剂中反应得到。其中，典型的醛或酮结构如下：
Figure BDA0004166000560000032
进一步地，在上述技术方案中，后处理操作为：反应结束，采用乙酸乙酯和水萃取反应产物，无水硫酸钠干燥后旋除溶剂，通过柱层析分离纯化，得到芳基仲胺类化合物。
本发明的有益效果
本发明以酮、对甲基苯磺酰肼和胺或者对甲苯磺酰腙衍生物与胺为主要原料，具有原料刺激性小、易于获得的特点。反应关键为通过缓慢释放供体/供体重氮物质，随后与多功能胺反应以实现N-H插入。反应过程在常温常压下，利用光催化反应合成N-H插入胺类化合物，不仅合成工艺简单，显著提高合成产率，而且反应后对环境污染小，绿色环保。原料廉价易得，操作简单，绿色环保，为N-H插入胺类化合物合成提供了一条新途径，同时该策略还可以应用于β-氨基酸的构建。
具体实施方式
下面结合本发明的实施例对本发明的实施作详细说明，以下实施例是在以本发明技术方案为前提下进行实施，给出了详细的实施方式和具体的操作过程，但本发明的保护范围不限于下述实施例。
实施例1条件优化实验：
在干燥反应管中，加入磁子和对甲苯磺酰腙衍生物1a(0.2mmol)，双排管置换氩气三次，接着加入4-氨基-2-氯吡啶2a(1.0mmol,5.0eq)、DBN(0.3mmol,1.5eq)与2.0mL二氯甲烷。密封后在427nm Kessil灯光源下(40W)光照，光源距离反应管约4厘米，风扇或者低温反应器降温，控制温度为25-35℃，6小时后停止反应，采用1,3,5-三甲氧基苯为内标计算产物3a收率(非分离收率)。
Figure BDA0004166000560000041
Figure BDA0004166000560000042
Figure BDA0004166000560000051
实施例2
在干燥反应管中，加入磁子和对甲苯磺酰腙衍生物1(0.2mmol)，双排管置换氩气三次，接着加入4-氨基-2-氯吡啶2a(1.0mmol,5.0eq)、DBN(0.3mmol,1.5eq)与2.0mL二氯甲烷。密封后在427nm Kessil灯光源下(40W)光照，光源距离反应管约4厘米，风扇或者低温反应器降温，控制温度为25-35℃，6小时后停止反应，乙酸乙酯和水萃取，无水硫酸钠干燥后旋除溶剂，通过柱层析分离纯化，得到N-H插入芳基仲胺类化合物3。不同反应底物结果如下所示：
Figure BDA0004166000560000052
Figure BDA0004166000560000061
实施例3
改变不同的反应原料1和2进行底物实验：
在干燥反应管中，加入磁子和对甲苯磺酰腙衍生物1(0.2mmol)，双排管置换氩气三次，接着加入胺2(1.0mmol,5.0eq)、DBN(0.3mmol,1.5eq)与2.0mL二氯甲烷。密封后在427nm Kessil灯光源下(40W)光照，光源距离反应管约4厘米，风扇或者低温反应器降温，控制温度为25-35℃，6小时后停止反应，乙酸乙酯和水萃取，无水硫酸钠干燥后旋除溶剂，通过柱层析分离纯化，得到N-H插入芳基仲胺类化合物3。反应结果如下：
Figure BDA0004166000560000071
以上已对本发明创造的较佳实施例进行了具体说明，但本发明创造并不限于所述实施例，熟悉本领域的技术人员在不违背本发明创造精神的前提下还可作出种种的等同的变型或替换，这些等同的变型或替换均包含在本申请权利要求所限定的范围内。

Claims (9)

1.一种光催化合成芳基仲胺类化合物的方法，其特征在于，包括如下步骤：以对甲苯磺酰腙衍生物1和胺2为原料，在碱存在下，有机溶剂中光照反应，得到芳基仲胺类化合物3；反应方程式如下：
Figure FDA0004166000550000011
其中：所述对甲苯磺酰腙衍生物1中，R1和R2各自独立选自H、C1-C4烷基、苄基及其取代物、苯基呋喃及其取代物、苯并噻吩及其取代物、吲哚及其取代物、苯基及其取代物、萘基及其取代物；取代物为C1-C4烷基、C1-C4烷氧基、C1-C4烷氧羰基烷氧基、亚甲基二氧基、Boc、卤素、苯氧基；或R1-R2一起通过碳、氧、硫或氮原子组成环状结构；所述胺2中，R3和R4各自独立选自H、C1-C6烷基、烯丙基、苄基、苯基/联苯基及其取代物、吡啶及其取代物、喹啉/喹喔啉及其取代物、嘧啶及其取代物；取代物为C1-C4烷基、C1-C4烷氧基、N-Boc哌嗪、卤素；或R1-R2一起通过碳、氧、硫或氮原子组成环状结构。
2.根据权利要求1所述光催化合成芳基仲胺类化合物的方法，其特征在于：所述碱选自DBU、DBN、DABCO、DTHP、Cs2CO3、K2CO3、K2PO4、Na2CO3或NaHCO3中的一种或多种。
3.根据权利要求1所述光催化合成芳基仲胺类化合物的方法，其特征在于：所述有机溶剂选自γ-戊内酯、二氯甲烷、乙腈、四氢呋喃及乙酸乙酯中的任意一种或多种组合。
4.根据权利要求1所述光催化合成芳基仲胺类化合物的方法，其特征在于：对甲苯磺酰腙衍生物1、胺2与碱摩尔比为1:1-10:1-3。
5.根据权利要求1所述光催化合成芳基仲胺类化合物的方法，其特征在于：反应温度为20-35℃；反应时间为4-20小时。
6.根据权利要求1所述光催化合成芳基仲胺类化合物的方法，其特征在于：光源波长为400-460nm；光源距离反应管为2-6厘米。
7.根据权利要求1-6任意一项所述光催化合成芳基仲胺类化合物的方法，其特征在于：反应在惰性氛围下进行。
8.根据权利要求1所述光催化合成芳基仲胺类化合物的方法，其特征在于：对甲苯磺酰腙衍生物1采用羰基化合物(醛或酮)与对甲苯璜酰肼在醇类溶剂中反应得到。
9.根据权利要求1所述光催化合成芳基仲胺类化合物的方法，其特征在于：反应结束，采用乙酸乙酯和水萃取反应产物，无水硫酸钠干燥后旋除溶剂，通过柱层析分离纯化，得到芳基仲胺类化合物。
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